Category: pyridine-derivatives

Reference of 1187236-18-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1187236-18-5 as follows.

Under the protection of -78 C and N2,To ethyl 7-bromoimidazo[1,2-a]pyridine-2-carboxylate (3.50 g, 13.0 mmol)Add in anhydrous DCM (80 mL) suspensionDiisobutylaluminum hydride (18.50 mL, 18.50 mmol, 1.0 M).The mixture was stirred at -78 C overnight.After the reaction is over, move to 0 C.And add water (0.75mL) in turn.15% NaOH aqueous solution (0.75mL)The reaction was quenched with water (2 mL).The resulting mixture was stirred at room temperature for 15 minutes.Then add Et2O (50 mL),EtOAc (50 mL) and Mg 2 SO 4 (20 g).Continue stirring for 15 minutes and filter again.The resulting filter cake was rinsed with EtOAc (200 mL).The filtrate was concentrated under reduced pressure.The residue obtained was purified by silica gel column chromatography (EtOAc /EtOAcTo give the title compound as a pale yellow solid (1.50g, 51% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1187236-18-5, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Peng Ju; Li Xiaobo; Zhang Tao; Hu Haiyang; Chen Wuhong; Bai Changlin; Ke Donghua; Chen Peng; (217 pag.)CN109776522; (2019); A;,
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Pyridine | C5H5N – PubChem

Electric Literature of 68325-15-5, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 68325-15-5, name is 3-Chloro-4-cyanopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To an ice-cooled solution of 2-methyl-2-(morpholin-4-yl)propan-1 -ol (4.00 g, 25.1 mmol) in THF (12.5 ml) under an argon atmosphere was added NaH 60% dispersion on mineral oil (1 .1 g, 27.4 mmol) slowly portionwise. The reaction mixture was stirred with ice-cooling for 1 h and a solution of 3-chloropyridine-4-carbonitrile (4.10 g, 29.6 mmol) in THF (64.5 ml) was added. The reaction was allowed to warm slowly to RT and stirred at this temperature for 16h. The reaction was then heated under reflux conditions for 2h. The reaction mixture was quenched with a sat. NH4CI solution and extracted with EtOAc. The organics were combined and washed with sat. NaCI, filtered through a hydrophobic filter and concentrated. The residue was crystallized with MTBE and collected by filtration to give the title compound (2 g, 35% yield) which was used without further purification.1H-NMR (400MHz, DMSO-d6): delta [ppm]= 8.75 (s, 1 H), 8.38 (d, 1 H), 7.78 (d, 1 H), 4.19 (s, 2H), 3.44 – 3.52 (m, 4H), 2.57 – 2.62 (m, 4H), 1.10 – 1 .23 (m, 6H).

According to the analysis of related databases, 68325-15-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; DANA FARBER CANCER INSTITUTE; SIEGEL, Stephan; SIEGEL, Franziska; SCHULZE, Volker; BERGER, Markus; GRAHAM, Keith; KLAR, Ulrich; KNUT, Eis; SUeLZLE, Detlev; BOeMER, Ulf; KORR, Daniel; PETERSEN, Kirstin; MOeNNING, Ursula; EBERSPAeCHER, Uwe; MOOSMAYER, Dieter; MEYERSON, Matthew; GREULICH, Heidi; KAPLAN, Bethany; HARB, Hassan, Youssef; DINH, Phi, Manh; (324 pag.)WO2019/81486; (2019); A1;,
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Pyridine | C5H5N – PubChem

Application of 100-54-9 , The common heterocyclic compound, 100-54-9, name is Nicotinonitrile, molecular formula is C6H4N2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: A solution of the appropriate cyanophenyl 1a-1j (0.1mol), hydroxylamine hydrochloride (0.2 mol), and TEA (0.2 mol) in methanol was stirred at room temperature for 1 h, then heated under reflux until the disappearance of the starting materials (TLC analysis). After cooling, the solvent was evaporated to dryness under reduced pressure to give the crude, which was dissolved in ethyl acetate (400 mL) and washed with brine (3×100 mL) and dried with Na2SO4. Ethyl acetate was evaporated under reduced pressure to yield the compounds 2a-2j.

The synthetic route of 100-54-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cai, Jin; Wei, Hongtao; Hong, Kwon Ho; Wu, Xiaoqing; Cao, Meng; Zong, Xi; Li, Lushen; Sun, Chunlong; Chen, Junqing; Ji, Min; European Journal of Medicinal Chemistry; vol. 96; (2015); p. 1 – 13;,
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Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 94166-64-0, name is 2-Chloro-6-nitropyridine, the common compound, a new synthetic route is introduced below. Formula: C5H3ClN2O2

Preparation of N-(3-(4-(6-Nitropyridin-2-yl)piperazin-l- yl)propyl)cyclohexanecarboxamideN-(3-(Piperazin-l-yl)propyl)cyclohexanecarboxamide (128 mg, 0.50 mmol), and 2- chloro-6-nitropyridine (79 mg, 0.50 mmol) were dissolved in dry acetonitrile (8 ml) in a 10 mL microwave tube and diisopropylethylamine (87 muL·, 0.50 mmol) added. The mixture was stirred and then heated in the microwave oven at 120C for 60 min. TLC (5% MeOH-EtOAc) showed the presence of 2 close running products of Rf 0.16 and 0.10. The reaction mixture was evaporated under reduced pressure to give a brown residue that was purified by chromatography on silica gel eluting with a 0-10% methanol in ethyl acetate gradient. The product was further purified by semi-preparative HPLC using a gradient of 50-95% methanol in water over 20 min (at) 18 ml/min (Gemini C18, 11 OA, 150 x 21.2 mm, 5 muiotaeta; Rt 10.8 min) to give the product (37 mg, 19%).LCMS: calcd for C19H29N5O3, 375.2; found 376.1 [M+H] . and 13C NMR were consistent with the structure.Purity was 96% by HPLC (UV 254nm).

The synthetic route of 94166-64-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GE HEALTHCARE LIMITED; MEDI-PHYSICS, INC.; NEWINGTON, Ian, Martin; WYNN, Duncan George; NAIRNE, Robert James Domett; GUILBERT, Benedicte; MANDAL, Subrata; JINTO, Jose; VARADARAJAN, Sunderaraman; RANGASWAMY, Chitralekha; BETTS, Helen; DAVIS, Rebecca; WO2011/150183; (2011); A1;,
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Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1004294-58-9, name is 6-Bromo-5-chloropyridin-2-amine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Bromo-5-chloropyridin-2-amine

A solution of N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-5-(2-chloro-5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)benzamido)-1-phenyl-1 H-pyrazole-3-carboxamide (Preparation 7, 500 mg, 0.80 mmol), 6-bromo-5-chloropyridin-2-amine (332 mg, 1.60 mmol) and potassium carbonate (221 mg, 1.60 mmol) in dioxane (10 mL) and water (5 mL) was degassed with nitrogen for 10 minutes before the addition of Pd(PP i3)4 (92 mg, 0.80 mmol). The reaction was heated to reflux for 2 hours. The reaction was diluted with EtOAc (20 mL) and water (20 mL). The aqueous phase was extracted with EtOAc (3 x 20 mL) and the combined organic layers were dried over MgS04 and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 40- 60% EtOAc in heptanes and dissolved in THF (2 mL). TBAF (1 M in THF, 96 uL, 0.096 mmol) was added and the reaction stirred at room temperature for 18 hours. The reaction was quenched by the addition of saturated aqueous NH4CI solution (10 mL) and extracted into EtOAc (3 x 10 mL). The combined organic layers were dried over MgS04 and concentrated in vacuo. The residue was purified using reverse phase chromatography eluting with 5-50% MeCN in water with 0.1 % ammonia followed by trituration with MeCN to afford the title compound (8 mg, 8%). 1 H NMR (400MHz, DMSO-d6): delta ppm 3.31-3.35 (2H, m), 3.50 (2H, q), 4.75 (t, 2H), 6.33 (s, 2H), 6.50 (d, 1 H), 6.90 (s, 1 H), 7.45-7.49 (m, 1 H), 7.53-7.62 (m, 5H), 7.70-7.76 (m, 2H), 8.16 (t, 1 H), 10.79 (br s, 1 H). MS m/z 51 1 [M+H]+

The synthetic route of 1004294-58-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BAGAL, Sharanjeet Kaur; CUI, Jingrong Jean; GREASLEY, Samantha Elizabeth; LUNNEY, Elizabeth Ann; MCALPINE, Indrawan James; NAGATA, Asako; NINKOVIC, Sacha; OMOTO, Kiyoyuki; SKERRATT, Sarah Elizabeth; STORER, Robert Ian; WARMUS, Joseph Scott; WO2015/159175; (2015); A1;,
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Synthetic Route of 53014-84-9, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.53014-84-9, name is 2-Methyl-5-formylpyridine, molecular formula is C7H7NO, molecular weight is 121.1366, as common compound, the synthetic route is as follows.

INTERMEDIATE 552- [(Hydroxy)(6-methylpyridin-3-yl)methyll acrylic acid ethyl esterTo a solution of 6-methylpyridine-3-carbaldehyde (5.0 g, 41 mmol) in ethyl acrylate (10 mL) at room temperature was added DABCO (1.0 g, 9 mmol), and the mixture was stirred overnight. The reaction mixture was concentrated in vacuo and the residue purified by column chromatography (Si02, hexane to 40%> ethyl acetate), to give the title compound (5.6 g, 62%) as a yellow oil. LCMS (ES+) 222.2 (M+H)+, RT 0.98 minutes.

The chemical industry reduces the impact on the environment during synthesis 53014-84-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; UCB PHARMA S.A.; PARTON, Andrew Harry; ALI, Mezher Hussein; BROOKINGS, Daniel Christopher; BROWN, Julien Alistair; FORD, Daniel James; FRANKLIN, Richard Jeremy; LANGHAM, Barry John; NEUSS, Judi Charlotte; QUINCEY, Joanna Rachel; WO2012/32334; (2012); A1;,
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Pyridine | C5H5N – PubChem

Related Products of 1822-51-1 , The common heterocyclic compound, 1822-51-1, name is 4-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Reference Example 1 Methyl 2-(pyridin-4-yl)methoxybenzoate (Reference Compound 1-(1)) To a solution of methyl salicylate (10 g, 66 mmol) and 4-chloromethylpyridine hydrochloride (11 g, 67 mmol) in N,N-dimethylformamide (150 mL) was added potassium carbonate (19 g, 140 mmol) under ice-cooling, and then the mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into an ice water and the aqueous layer was extracted with ethyl acetate (150 mL, twice). The ethyl acetate layer was washed with a saturated brine solution (200 mL), dried over anhydrous sodium sulfate, and concentrated under a reduced pressure to dryness, and the resultant residue was purified with a silica gel column chromatography (hexane/ethyl acetate) and dried to give 12 g (75 %) of the titled compound as a colorless solid. 1H-NMR (300MHz, CDCl3) delta 3.93 (s, 3H), 5.19(s, 2H), 6.97(d, J=8.3Hz, 1H), 7.04(t, J=7.5Hz, 1H), 7.43-7.50(m, 3H), 7.87(dd, J=7.9, 1.8Hz, 1H), 8.63(d, J=6.1Hz, 2H) The following Reference Compounds 1-(2) to (8) were obtained by a production method similar to that of Reference Compound 1-(1) using compounds selected from known compounds, 4-chloromethylquinoline (CAS#5632-17-7;) and 2-acetamido-4-methanesulfonyloxymethylpyridine (CAS#864461-12-1;) and commercially available compounds.

The synthetic route of 1822-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Santen Pharmaceutical Co., Ltd; EP2128156; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.82454-61-3, name is 5-Ethynylpyridin-2-amine, molecular formula is C7H6N2, molecular weight is 118.14, as common compound, the synthetic route is as follows.Recommanded Product: 82454-61-3

A solution of 7 (36.0 g), copper(I) iodide (334 mg), bis-(triphenylphosphine)-palladium(II)-dichloride (557 mg), triphenylphosphine (414 mg) and triethylamine (25.5 mE) in MeTHF (145 mE) was treated at 70-75°C. within 2 to 3 hours with a MeTHF solution of 1.1 equiv. of 5-ethynylpyridin-2- ylamine (9) (prepared according to Example 11) and the resulting suspension was subsequently stirred at 70-75°C. for additional 5-10 hours. The mixture was cooled to 30° C. and treated with water (150 mE) and 25percent aqueous ammonium hydroxide solution (30 mE). The biphasic mixture was stirred for 30 minutes and the layers were then allowed to separate for 20 minutes. The aqueous layer was removed and the MeTHF layer was washed twice with a mixture of water (150 mE) and 25percent aqueous ammonium hydroxide solution (30 The MeTHF layer was subsequently washed with water (3x 150 mE). The organic layer was polish filtered, and the filtrate was treated with n-tributylphosphine (1.00 mE). MeTHF was then distilled off and completely replaced by isopropanol (500 mE in total) at atmospheric pressure. The resulting suspension (ca. 250 mE) was heated to reflux and stirred at reflux for 2 hours then cooled to room temperature overnight. The product was filtered and washed with two portions of isopropanol (50 mE). The wet crystals were dried at 50° C. and <30 mbar until constant weight affording 29.45 g (84percent yield based on 7) of compound A as red crystals with a purity of 99.7percent (HPEC, area-percent). At the same time, in my other blogs, there are other synthetic methods of this type of compound,82454-61-3, 5-Ethynylpyridin-2-amine, and friends who are interested can also refer to it. Reference:
Patent; Hoffmann-La Roche Inc; Bachmann, Stephan; Bailey, Daniel; Brice, Jodie; Cedilote, Miall; Dong, Zhiming; Hildbrand, Stefan; Miller, Doreen; Spurr, Paul; Srivastava, Amit; Wichmann, Juergen; Woltering, Thomas; Yang, Jason; Zhang, Pingsheng; US2013/85278; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 94446-97-6, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 94446-97-6, name is 2-Bromo-3-(bromomethyl)pyridine. A new synthetic method of this compound is introduced below.

General procedure: A mixture of quinazolinone 19a or 19b-c (1.0 mmol) and NaH in DMF was maintained under N2 for 5 min. The appropriate haloderivative or aryloxirane was added (1.0mmol) andthe mixture was microwave irradiated at 120 C (power set point 250W; ramp time 30 sec; hold time 5 min). After cooling, the mixture was poured insat. NH4Cl solution (30 mL) and the obtained precipitate wascollected by filtration. The solid was purified by crystallization to give thetitle compounds.3-[(2?-Bromopyridin-3?-yl)methyl]-6,7-dimethoxyquinazolin-4(3H)-one (1). From 19a and 2-bromo-3-bromomethylpyridine:yield 26% (EtOAc); mp 282C;1H NMR (300 MHz, DMSO-d6): delta 8.43 (s, 1 H, 2-H); 8.32 (dd, J = 3.4 and 2.8 Hz, 1 H, 6?-H), 7.45 (s,1 H, 5-H or 10-H), 7.41-7.39 (m, 2 H, 4?-H and 5?-H), 7.20 (s, 1 H, 5-H or10-H), 5.19 (s, 2 H, NCH2), 3.93 (s, 3 H, OCH3), 3.86 (s,3 H, OCH3). 13CNMR (75 MHz, DMSO-d6): delta 159.39, 154.64, 149.02, 148.84, 146.65, 144.10,141.39, 137.22, 133.00, 123.60, 114.54, 107.99, 105.02, 55.99, 55.66, 48.75. Anal.calcd. for C16H14BrN3O3: C, 51.08;H, 3.75; Br, 21.24; N, 11.17; found: C, 51.10; H, 3.77; Br, 21.20; N, 11.19.HRMS (ESI-TOF) for C16H15BrN3O3 [M+ H]+: calcd.: 376.0291, found: 376.0296.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,94446-97-6, 2-Bromo-3-(bromomethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Article; Marzaro, Giovanni; Castagliuolo, Ignazio; Schirato, Giulia; Palu’, Giorgio; Dalla Via, Martina; Chilin, Adriana; Brun, Paola; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 416 – 425;,
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Reference of 16665-38-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 16665-38-6, name is (4-Methoxypyridin-2-yl)methanol, molecular formula is C7H9NO2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

4-Methoxypyridine-2-carbaldehyde, used as starting material was prepared as follows:- Manganese(IV) oxide (2.412 mL, 139.42 mmol, 4eq) was added portionwise to (4- methoxypyridin-2-yl)methanol (4.85g, 34.85 mmol, leq) in ethyl acetate (15OmL). The resulting mixture was stirred at 80 0C for 2 h. The hot reaction mixture was filtered through celite. The resulting mixture was evaporated to dryness to afford desired A- methoxypyridine-2-carbaldehyde (3.01 g, 21.93 mmol, 62.9 %). IH NMR (400.132 MHz, DMSO) delta 3.93 (3H, s), 7.27 (IH, m), 7.44 (IH, d), 8.63 (IH, d), 9.96 (IH, s)

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 16665-38-6, (4-Methoxypyridin-2-yl)methanol.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/56886; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem